Difference between revisions of "Dimercaprol"
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| − | '''Dimercaprol''' ([[International Nonproprietary Name|INN]]) or '''British anti-Lewisite''' (abbreviated '''BAL'''), is a compound developed by British biochemists at [[Oxford University]] during [[World War II]].<ref>{{cite web |url = http://www.chm.bris.ac.uk/motm/bal/development.html |author= Domingo Tabangcura, Jr., G. Patrick Daubert|title=British anti-Lewisite}}</ref><ref>Peters R, Stocken L, Thompson R. (1945) British Anti-Lewisite (BAL). Nature 156: 616-619</ref> It was developed secretly as an antidote for [[Lewisite]], the now-obsolete [[arsenic]]-based [[chemical warfare agent]].<ref>{{cite web |url = http://www.chm.bris.ac.uk/motm/bal/development.html |author= Domingo Tabangcura, Jr., G. Patrick Daubert|title=British anti-Lewisite}}</ref> Today, it is used medically in treatment of [[arsenic]], [[Mercury (element)|mercury]], [[gold]] and [[lead]], and other [[toxic metal|toxic metal poisoning]].<ref>{{cite web |url = http://www.drugs.com/dict/dimercaprol.html |title=Dimercaprol}}</ref> In addition, it has in the past been used for the treatment of [[Wilson's disease]], a genetic disorder in which the body tends to retain [[copper]].<ref>{{cite journal |author=Denny-Brown D, PORTER H |title=The effect of BAL (2,3-dimercaptopropanol) on hepatolenticular degeneration (Wilson's disease) |journal=N. Engl. J. Med. |volume=245 |issue=24 |pages=917–25 |year=1951 |month=December |pmid=14882450}}</ref> | + | '''Dimercaprol''' ([[International Nonproprietary Name|INN]]) or '''British anti-Lewisite''' (abbreviated '''BAL'''), is a compound developed by British biochemists at [[Oxford University]] during [[World War II]].<ref>{{cite web |url = http://www.chm.bris.ac.uk/motm/bal/development.html |author= Domingo Tabangcura, Jr., G. Patrick Daubert|title=British anti-Lewisite}}</ref><ref>Peters R, Stocken L, Thompson R. (1945) British Anti-Lewisite (BAL). Nature 156: 616-619</ref> It was developed secretly as an antidote for [[Lewisite]], the now-obsolete [[arsenic]]-based [[chemical warfare agent]].<ref>{{cite web |url = http://www.chm.bris.ac.uk/motm/bal/development.html |author= Domingo Tabangcura, Jr., G. Patrick Daubert|title=British anti-Lewisite}}</ref> Today, it is used medically in treatment of [[arsenic]], [[Mercury (element)|mercury]], [[gold]] and [[lead]], and other [[toxic metal|toxic metal poisoning]].<ref>{{cite web |url = http://www.drugs.com/dict/dimercaprol.html |title=Dimercaprol}}</ref> In addition, it has in the past been used for the treatment of [[Wilson's disease]], a genetic disorder in which the body tends to retain [[copper]].<ref>{{cite journal |doi=10.1056/NEJM195112132452401 |author=Denny-Brown D, PORTER H |title=The effect of BAL (2,3-dimercaptopropanol) on hepatolenticular degeneration (Wilson's disease) |journal=N. Engl. J. Med. |volume=245 |issue=24 |pages=917–25 |year=1951 |month=December |pmid=14882450}}</ref> |
== Biochemical function == | == Biochemical function == | ||
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[[pl:Dimerkaprol]] | [[pl:Dimerkaprol]] | ||
[[ru:Димеркаптопропансульфонат натрия]] | [[ru:Димеркаптопропансульфонат натрия]] | ||
| + | [[zh:二巯基丙醇]] | ||
[[Category:2Fix]] | [[Category:2Fix]] | ||
Latest revision as of 19:14, 21 September 2010
 | This article includes a list of references, related reading or external links, but its sources remain unclear because it lacks inline citations. Please improve this article by introducing more precise citations. (May 2008) |
| File:Dimercaprol.svg | |
| File:Dimercaprol-3D-balls.png | |
| Systematic (IUPAC) name | |
|---|---|
|
(RS)-2,3-disulfanylpropan-1-ol | |
| Identifiers | |
| CAS Number | 59-52-9 |
| ATC code | V03AB09 (WHO) |
| PubChem | CID 3080 |
| ChemSpider | 2971 |
| Synonyms | 2,3-Dimercaptopropanol |
| Chemical data | |
| Formula | C3H8OS2 |
| Molar mass | 124.23[[Script error: No such module "String".]] |
| Script error: No such module "collapsible list". | |
| (verify) | |
Dimercaprol (INN) or British anti-Lewisite (abbreviated BAL), is a compound developed by British biochemists at Oxford University during World War II.[1][2] It was developed secretly as an antidote for Lewisite, the now-obsolete arsenic-based chemical warfare agent.[3] Today, it is used medically in treatment of arsenic, mercury, gold and lead, and other toxic metal poisoning.[4] In addition, it has in the past been used for the treatment of Wilson's disease, a genetic disorder in which the body tends to retain copper.[5]
Biochemical function
Arsenic and some other heavy metals act by chemically reacting with adjacent thiol residues on metabolic enzymes, creating a chelate complex that inhibits the affected enzyme's activity[6]. Dimercaprol competes with the thiol groups for binding the metal ion, which is then excreted in the urine.[citation needed]
Dimercaprol is itself toxic, with a narrow therapeutic range and a tendency to concentrate arsenic in some organs. Other drawbacks include the need to administer it by painful intramuscular injection [7]. Serious side effects include nephrotoxicity and hypertension.
Dimercaprol has been found to form stable chelates in vivo with many other toxic metals including inorganic mercury, antimony, bismuth, cadmium, chromium, cobalt, gold, and nickel. However, it is not necessarily the treatment of choice for toxicity to these metals. Dimercaprol has been used as an adjunct in the treatment of the acute encephalopathy of lead toxicity. It is a potentially toxic drug, and its use may be accompanied by multiple side effects. Although treatment with dimercaprol will increase the excretion of cadmium, there is a concomitant increase in renal cadmium concentration, so that its use in case of cadmium toxicity is to be avoided. It does, however, remove inorganic mercury from the kidneys; but is not useful in the treatment of alkylmercury or phenyl mercury toxicity. Dimercaprol also enhances the toxicity of selenium and tellurium, so it is not to be used to remove these metals from the body.[citation needed]
See also
References
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<references />, or <references group="..." />- Casarett and Doull's Toxicology, the basic science of poisons [Incomplete reference?]
es:Dimercaprol fr:BAL - British Anti Lewisite nl:Dimercaprol ja:ジメルカプロール pl:Dimerkaprol ru:Димеркаптопропансульфонат натрия
zh:二巯基丙醇- ↑ Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite".
- ↑ Peters R, Stocken L, Thompson R. (1945) British Anti-Lewisite (BAL). Nature 156: 616-619
- ↑ Domingo Tabangcura, Jr., G. Patrick Daubert. "British anti-Lewisite".
- ↑ "Dimercaprol".
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Goldman M, Dacre JC. (1989) Lewisite: its chemistry, toxicology, and biological effects. Rev Environ Contam Toxicol 110: 75-115
- ↑ Mückter H, Liebl B, Reichl FX et al. (1997) Are we ready to replace dimercaprol (BAL) as an arsenic antidote? Human and Experimental Toxicology 16: 460-465
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